ChemicalBook CAS DataBase List tert-butyl azidoformate

tert-butyl azidoformate synthesis

5synthesis methods

Product Name:tert-butyl azidoformate
CAS Number:1070-19-5
Molecular formula:C5H9N3O2
Molecular Weight:143.1439

tert-Butyl chloroformate was prepared in solution as follows. Dry phosgene was introduced into a solution of 18 g (0.24 mol) of tert-butyl alcohol in 500 ml of anhydrous ether until about 52 g (0.5 mol) had been absorbed and the mixture was cooled in a Dry Ice-acetone bath. Then a solution of 20 g (0.28 mol) of pyridine in 200 ml of anhydrous ether was added dropwise with vigorous stirring. The reaction mixture was stored overnight in a Dry Ice box. The precipitated pyridine hydrochloride was filtered and the volume of the filtrate was reduced to -70 ml at reduced pressure with cooling in an icewater bath.This cold solution of tert-butyl chloroformate was added over 30 min to a vigorously stirred solution of 31.6 g (0.2 mol) of tetramethylguanidinium azide in 200 ml of chloroform; the temperature was kept at 0°C throughout the addition. The bath was removed and the reaction mixture stirred for an additional hour and then poured into 500 nil of ice water containing -2 ml of acetic acid. Extraction with two 60-ml portions of ether followed by careful evaporation of the dried (magnesium sulfate) organic phase gave tert-butyl azidoformate as a pale amber liquid in quantitative yield.
The Direct Preparation of tert-Butyl Azidoformate

870-46-2 Synthesis

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1070-19-5
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Yield:1070-19-5 97%

Reaction Conditions:

with potassium hydrogencarbonate;sodium nitrite in water;acetic acid

Steps:

4.a (a)
(a) t-Butyl azidoformate 60 g of t-butyloxycarbonylhydrazine are dissolved at about 30° in 48 ml of acetic acid; the solution is diluted with 72 ml of water and cooled to -2° with an ice-salt bath. 34.6 g of sodium nitrite, dissolved in 48 ml of water, are added dropwise to the mixture, whilst stirring magnetically and keeping the temperature in the region of 0°. The stirring is continued for 1 hour 30 minutes after the end of the addition, the mixture is diluted with 60 ml of water and the supernatant organic phase is decanted. The aqueous phase is extracted 3 or 4 times with pentane and these extracts are mixed with the 1st organic phase. The solution obtained is washed 5 times with 30 ml of water, 3 times with 60 ml of a N solution of potassium bicarbonate and finally 3 times with 60 ml of water. After drying over magnesium sulphate, the solvent is evaporated off at ordinary temperature. 59 g (yield 97%) of crude t-butyl azidoformate, which is used without purification, are obtained. This compound boils at 34°/12 mm Hg.

References:

Synthelabo US4134991, 1979, A

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24608-52-4 Synthesis